The Template Effect

  • George W. Gokel
  • Stephen H. Korzeniowski
Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY, volume 13)


It has been axiomatic for many years that large rings must be prepared under high dilution conditions so that the probability of the two ends meeting exceeds the probability of linear polymer formation7. It therefore seems remarkable that many of the syntheses of macrocyclic polyethers which have been reported involve less than dilute if not very concentrated conditions18. The success of these large-ring intramolecular SN2 reactions is generally attributed to the operation of a “template” effect during crown synthesis.


Crown Ether Macrocyclic Lactone Triethylene Glycol Lithium Cation Tetrahedron Letter 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Chan, L. L., Wong, K. H. and Smid, J.: J. Am. Chem. Soc. (1970) 92, 1955CrossRefGoogle Scholar
  2. 2.
    Chastrette, M. and Chastrette, F.: J. Chem. Soc. Chem. Commun. (1973) 534Google Scholar
  3. 3.
    Cook, F. L., Caruso, T. C., Byrne, M. P., Bowers, C. W., Speck, D. H. and Liotta, C. L.: Tetrahedron Letters (1974) 4092Google Scholar
  4. 4.
    Dale, J. and Daasvatn, K.: J. Chem. Soc. Chem. Commun. (1976) 295Google Scholar
  5. 5.
    Dale, J. and Kristiansen, P. O.: J. Chem. Soc. Chem. Commun. (1971) 670Google Scholar
  6. 6.
    Desvergne, J. P. and Bouas-Laurent, H.: J. Chem. Soc. Commun. (1978)403 Google Scholar
  7. 7.
    Eliel, E. L.: Stereochemistry of Carbon Compounds. McGraw Hill, New York 1962, 198 and references thereinGoogle Scholar
  8. 8.
    Fenton, D. E., Cook, D. H. and Nowell, I. W.: J. Chem. Soc. Chem. Commun. (1977) 274Google Scholar
  9. 9.
    Gray, R. T., Reinhoudt, D. N., Smit, C. J. and Veenstra, I.: Reel Trav. Chem. Pays-Bas (1976) 95, 258CrossRefGoogle Scholar
  10. 10.
    Greene, R. N.: Tetrahedron Letters (1972) 1793Google Scholar
  11. 11.
    Izatt, R. M., Terry, R. E., Haymore, B. L., Hansen, L. D., Dalley, N. K., Avondet, A. G. and Christensen, J. J.: J. Am. Chem. Soc. (1976) 98, 7620CrossRefGoogle Scholar
  12. 12.
    Kawamura, N., Miki, M., Ikeda, I. and Okahara, M.: Tetrahedron Letters (1979) 535Google Scholar
  13. 13.
    Lehn, J. M., Vierling, P., Hayward, R. G: J. Chem. Soc. Chem. Commun. (1979) 296Google Scholar
  14. 14.
    Madan, K. and Cram, D. J.: J. Chem. Soc. Chem. Commun. (1975) 427Google Scholar
  15. 15.
    Mandolini, L. and Masci, B.: J. Am. Chem. Soc. (1977) 99, 7709CrossRefGoogle Scholar
  16. 16.
    Mandolini, L. and Masci, B.: Synth. Commun. (1979) 9, 851CrossRefGoogle Scholar
  17. 17.
    Newkome, G. R., Kawato, T. and Benton, W. H.: J. Org. Chem. (1980) 45, 626CrossRefGoogle Scholar
  18. 18.
    Pedersen, C. J.: J. Am. Chem. Soc. (1967) 89, 7017CrossRefGoogle Scholar
  19. 19.
    Rastetter, W. H., Phillion, D. P.: Tetrahedron Letters (1979) 1469Google Scholar
  20. 20.
    Reinhoudt, D. N., de Jong, F. and Tomassen, H. P. M.: Tetrahedron Letters (1979) 2067Google Scholar
  21. 21.
    Reinhoudt, D. H., Gray, R. T., Smit, C. J. and Veenstra, I.: Tetrahedron (1976) 32, 1161CrossRefGoogle Scholar
  22. 22.
    Ugelstad, J., Mork, P. C. and Jensen, B.: Acta Chem. Scand. (1963) 27, 1455CrossRefGoogle Scholar
  23. 23.
    Vögtle, F. and Weber, E.: Angew. Chem. Int. Ed. Engl. (1979) 18, 753CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1982

Authors and Affiliations

  • George W. Gokel
    • 1
  • Stephen H. Korzeniowski
    • 2
  1. 1.Department of ChemistryUniversity of MarylandCollege ParkUSA
  2. 2.Chemicals and Pigments Department, Jacson LaboratoryE. I. Du Pont de Nemours Co., Inc.DeepwaterUSA

Personalised recommendations